Polyfluoroorganoboron‐Oxygen Compounds. 2 [1] Base‐catalysed Hydrodeboration of Polyfluorophenyl(dihydroxy)boranes

作者: H.-J. Frohn , N. Y. Adonin , V. V. Bardin , V. F. Starichenko

DOI: 10.1002/1521-3749(200213)628:13<2834::AID-ZAAC2834>3.0.CO;2-2

关键词: BoranesSubstituentBoraneNuclear magnetic resonance spectroscopyBase (chemistry)StereochemistryPhenyl groupMedicinal chemistryChemistryPyridineFluorine

摘要: Polyfluorinated phenyl(dihydroxy)boranes C6H5-nFnB(OH)2 (n = 3 — 5) underwent hydrodeboration (formal replacement of the (dihydroxy)boryl group by hydrogen) in presence bases (MeOH, 33 % H2O—MeOH, KOH (1 equiv.)/33 pyridine and 9 D2O—pyridine) formed fluoroaromatic compounds ArH or ArD, respectively. The rate reaction depends on number fluorine atoms phenyl position atoms, relative to B(OH)2 substituent. Polyfluororganische Bor-Sauerstoff Verbindungen. 2 [1] Die Hydrodeborierung von Polyfluorphenyl(dihydroxy)boranen unter basischen Bedingungen Polyfluorierte Phenyl(dihydroxy)borane unterliegen Gegenwart Basen Aquiv.)/33 Pyridin und D2O—Pyridin) einer Hydrodeborierungsreaktion (formaler Ersatz der (Dihydroxy)borylgruppe durch Wasserstoff) bilden die entsprechenden Fluoraromaten oder ArD. Reaktionsgeschwindigkeit hangt dabei Anzahl Fluoratome Arylgruppe relativen Stellung zum B(OH)2-Substituenten ab.

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